1,3,3-Trinitroazetidine

1,3,3-Trinitroazetidine
Names
	IUPAC name 1,3,3-trinitroazetidin
	Other names TNAZ
Identifiers
CAS Number	97645-24-4 ;
3D model (JSmol)	Interactive image;
ChemSpider	7969893 ;
PubChem CID	9794126;
UNII	41T9FAH22H ;
CompTox Dashboard (EPA)	DTXSID20913764 ;
	InChI InChI=1S/C3H4N4O6/c8-5(9)3(6(10)11)1-4(2-3)7(12)13/h1-2H2 Key: ZCRYIJDAHIGPDQ-UHFFFAOYSA-N;
	SMILES C1C(CN1[N+](=O)[O-])([N+](=O)[O-])[N+](=O)[O-];
Properties
Chemical formula	C3H4N4O6
Molar mass	192.09 g/mol
Appearance	pale yellow orthorhombic crystals
Density	1.84 g/cm3
Melting point	101[1] °C (214 °F; 374 K)
Boiling point	252[1] °C (486 °F; 525 K)
Hazards
Flash point	unknown
Autoignition; temperature	unknown
Explosive data
Shock sensitivity	unknown
Friction sensitivity	unknown
Detonation velocity	9597 m/s[2]
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

1,3,3-Trinitroazetidine (TNAZ) is a highly energetic heterocyclic compound that has been considered as a potential replacement for TNT because of its low melting point (101 °C) and good temperature stability (up to 240 °C). TNAZ was first synthesized by Archibald et al. in 1983 in work published in 1990.[3] Several synthesis routes are known and bulk production of several hundred kilogram batches has been demonstrated at Los Alamos National Laboratory.[4][1][5]

Properties

TNAZ forms pale yellow crystals with a melting point of 101 °C. The compound crystallizes in an orthorhombic lattice with the space group Pbca. Thermolysis occurs starting around 240 °C - 250 °C with decomposition products that include nitrogen dioxide, nitric oxide, nitrous acid, carbon dioxide and formaldehyde. As far as energetic properties, it is roughly 30% more energetic than TNT and has a heat of explosion of ~6343 kJ/kg, a detonation velocity of ~9000 m/s, and a detonation pressure of 36.4 GPa.[6]

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References

Viswanath, Dabir S.; Ghosh, Tushar K.; Boddu, Veera M. (2018). 1,3,3-Trinitroazetidine (TNAZ). Emerging Energetic Materials: Synthesis, Physicochemical, and Detonation Properties. pp. 293–307. doi:10.1007/978-94-024-1201-7_11. ISBN 978-94-024-1199-7.
Simpson, R.L.; Garza, R.G.; Foltz, M.F.; Ornellas, D.L.; Utriew, P.A. (14 December 1994). Characterization of TNAZ (PDF) (Technical report). Office of Scientific and Technical Information (OSTI). doi:10.2172/71573. OSTI 71573.
Archibald, T. G; Gilardi, Richard; Baum, K; George, Clifford (1990). "Synthesis and x-ray crystal structure of 1,3,3-trinitroazetidine". The Journal of Organic Chemistry. 55 (9): 2920–2924. doi:10.1021/jo00296a066.
Coburn, Michael D.; Hiskey, Michael A.; Archibald, Thomas G. (January 1998). "Scale-up and waste-minimization of the Los Alamos process for 1,3,3-trinitroazetidine (TNAZ)". Waste Management. 17 (2–3): 143–146. doi:10.1016/S0956-053X(97)10013-7.
Jalový, Zdenek; Zeman, Svatopluk; Suceska, Muhamed; Vávra, Pave; Dudek, Kamil; Rajic, Masa (1 June 2001). "1,3,3-trinitroazetidine (TNAZ). Part I. Syntheses and properties". Journal of Energetic Materials. 19 (2): 219–239. doi:10.1080/07370650108216127. ISSN 0737-0652.
Axenrod, Theodore; Watnick, Clara; Yazdekhasti, Hamid; Dave, Paritosh R (1993). "Synthesis of 1,3,3-trinitroazetidine". Tetrahedron Letters. 34 (42): 6677–6680. doi:10.1016/S0040-4039(00)61673-8.

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[book-1] Viswanath, Dabir S.; Ghosh, Tushar K.; Boddu, Veera M. (2018). 1,3,3-Trinitroazetidine (TNAZ). Emerging Energetic Materials: Synthesis, Physicochemical, and Detonation Properties. pp. 293–307. doi:10.1007/978-94-024-1201-7_11. ISBN 978-94-024-1199-7.

[2] Simpson, R.L.; Garza, R.G.; Foltz, M.F.; Ornellas, D.L.; Utriew, P.A. (14 December 1994). Characterization of TNAZ (PDF) (Technical report). Office of Scientific and Technical Information (OSTI). doi:10.2172/71573. OSTI 71573.

[arch-3] Archibald, T. G; Gilardi, Richard; Baum, K; George, Clifford (1990). "Synthesis and x-ray crystal structure of 1,3,3-trinitroazetidine". The Journal of Organic Chemistry. 55 (9): 2920–2924. doi:10.1021/jo00296a066.

[4] Coburn, Michael D.; Hiskey, Michael A.; Archibald, Thomas G. (January 1998). "Scale-up and waste-minimization of the Los Alamos process for 1,3,3-trinitroazetidine (TNAZ)". Waste Management. 17 (2–3): 143–146. doi:10.1016/S0956-053X(97)10013-7.

[5] Jalový, Zdenek; Zeman, Svatopluk; Suceska, Muhamed; Vávra, Pave; Dudek, Kamil; Rajic, Masa (1 June 2001). "1,3,3-trinitroazetidine (TNAZ). Part I. Syntheses and properties". Journal of Energetic Materials. 19 (2): 219–239. doi:10.1080/07370650108216127. ISSN 0737-0652.

[Axenrod-6] Axenrod, Theodore; Watnick, Clara; Yazdekhasti, Hamid; Dave, Paritosh R (1993). "Synthesis of 1,3,3-trinitroazetidine". Tetrahedron Letters. 34 (42): 6677–6680. doi:10.1016/S0040-4039(00)61673-8.